Like so many others, I first tried on mom's things when I was 4. The week previously I had gotten into my dad's old WWII Navy stuff. They caught me but it was no big thing. Now I wanted to get into mom's things. Got as far as lipstick and one stocking I think. Mom caught me. WHOLE different reaction!
First time I ever saw her cry! She made me promise never to do it again. Well I intended to keep that promise, but of course I couldn't. I did feel very guilty every time I got into her things again. She also became paranoid that I might become gay, or a crossdresser, or a transsexual. So lots of things that I wanted to do suddenly became off-limits to me. Like when I wanted a pair of white gloves to play traffic cop, it took a long time to get those!So began the stealth years. She never caught me again, but she tried. I think she knew I was still getting into her things, but she could never prove it. I learned to put drawers back exactly as I had found them, and so on.
At the age of 16 I bought my first stuff--a pair of stockings from the dime store. I wore them that evening in my room (with a bathrobe), but I knew I would have to throw them out--Mom searched everywhere and someplace like under the mattress would not be safe for a day! So I made my first purge that night.
And that was the pattern through college and my 20s. I would buy something, take it home, try it on, look in the mirror, relieve myself, feel very guilty, and purge it with promises to myself and God never, never to do that again. I bought mostly hosiery but occasionally other things. And I look back on how much money I threw away. My friends were buying stereos, records, etc. and I bought and purged.
When I was a senior in high school I had my first serious girlfriend. She was attractive and nice and I loved her. She also had two things rare in teenage girls--great taste in clothes and the money to buy them. My crossdressing interest stopped cold as I paid attention to what she was wearing. Too much attention--she mistook it for my being too dependent and clingy and that eventually was one of the things that killed our relationship. What I was doing, of course, was transferring all my crossdressing onto her. But I didn't understand that at the time. I assumed that I had found the cure for crossdressing, someone to love. My crossdressing, then, must be just because of loneliness. Find the right girl and it would go away again.
So when I found another girlfriend in college, and my crossdressing desires came back (she wasn't the clothes horse the first girl had been), I "knew" that I didn't really love her and broke up with her. She was the sweetest girl I had ever met and I was really dumb!
I met the girl who would become my wife when I was in my late 20s. Our relationship grew slowly, not because there wasn't interest, but because she had been burned by a boyfriend who wanted things to develop too quickly. I think he asked her to marry him on their second date. This worked out well because until we were really in love, I could still crossdress. And once we were in love, the crossdressing stopped. I asked her to marry me and six months later we were married.
About nine months into marriage, the desire to crossdress started to return. I knew I loved her deeply and she loved me. As a young married couple, we had access to sex. So I didn't understand why I wanted to crossdress again. What I did know was that I sure wasn't going to divorce her over this. Whatever was wrong, we could work it out.
So I came out to her. She was initially shocked but soon came to be very accepting. I asked her if we could try both wearing pantyhose in bed during foreplay. She agreed to it and we both enjoyed it. We've done it many, many times since.
After it was over, I should purge, right? Didn't I always? Well, that seemed really dumb, so for the first time, I put my pantyhose away in the drawer and left them there. I remember wondering if that would be safe! Would my mother break into our apartment and find them, I worried. Would my wife throw them away? When I got home that night they were still there. Amazing!That was the beginning of my coming out of the closet. I began, very slowly at first, to dress more and more. Before lovemaking. After lovemaking. Around the house. At first it was just pantyhose with sexy at-home male outfits. I think my first skirt was about 15 years later. Of course I was working all these years. I was a computer programmer and the hours were long. We bought a home. There wasn't much time to think about crossdressing.
The first time I dressed fully was Halloween about 7 years ago. All those years, the idea of dressing fully as a woman and going out had never seriously occurred to me! I assumed, since I knew nothing about makeup (and my wife never wore it), and am no great actor, I didn't have a chance. I would look like some silly overgrown boy in a dress and everyone would laugh. But I found other crossdressers on the internet and they all talked about it, so I knew I should give it a try. I tried it, and no one laughed! I loved it! I tried it again a few weeks later. It wasn't Halloween now, but I had heard about a friendly place, Tuesday nights at Tommy Tang's on Melrose. It worked again and I had an even better time!
I've been going out ever since. My dressing became more and more of the time, and for the past five years has been virtually full time.
